Synonym
Grifolic acid; Ilicicolinic Acid B
IUPAC/Chemical Name
2,4-Dihydroxy-6-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoic acid
InChi Key
QPIZDZGIXDKCRC-JTCWOHKRSA-N
InChi Code
InChI=1S/C23H32O4/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-19-20(24)14-18(5)21(22(19)25)23(26)27/h8,10,12,14,24-25H,6-7,9,11,13H2,1-5H3,(H,26,27)/b16-10+,17-12+
SMILES Code
O=C(O)C1=C(C)C=C(O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)=C1O
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Grifolic acid acts as an agonist of the free fatty acid receptor (FFAR4/GPR120).
In vitro activity:
Grifolic acid (20 μmol/L) inhibited the viability of GH3 cells after 1 h incubation and resulted in total cell death 6 h later. It showed a dose- and time-dependent inhibition of GH3 cell viability from 2.5 μmol/L to 20 μmol/L in 24 h incubation (Fig. 1).
Reference: BMC Pharmacol Toxicol. 2018 May 30;19(1):26. https://pubmed.ncbi.nlm.nih.gov/29843779/
In vivo activity:
In the present study, the effects of grifolic acid on macrophages were observed in mouse RAW264.7 cells. It was demonstrated that grifolic acid (2.5‑20 µmol/l) treatment reduced RAW264.7 cell viability in a dose‑ and time‑dependent manner. The number of apoptotic cells significantly increased following grifolic acid treatment compared with the untreated control cells. Grifolic acid treatment resulted in a significant decrease in cellular adenosine 5'‑triphosphate (ATP) content in RAW264.7 cells.
Reference: Mol Med Rep. 2018 Feb;17(2):3281-3287. https://pubmed.ncbi.nlm.nih.gov/29257254/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
68.6 |
184.23 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
372.51
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Zhao Y, Zhang L, Yan A, Chen D, Xie R, Liu Y, Liang X, Zhao Y, Wei L, Yu J, Xu X, Su X. Grifolic acid induces GH3 adenoma cell death by inhibiting ATP production through a GPR120-independent mechanism. BMC Pharmacol Toxicol. 2018 May 30;19(1):26. doi: 10.1186/s40360-018-0215-4. PMID: 29843779; PMCID: PMC5975534.
2. Zhao Y, Zhang H, Yan A, Zhu J, Liu K, Chen D, Xie R, Xu X, Su X. Grifolic acid induces mitochondrial membrane potential loss and cell death of RAW264.7 macrophages. Mol Med Rep. 2018 Feb;17(2):3281-3287. doi: 10.3892/mmr.2017.8218. Epub 2017 Dec 7. PMID: 29257254.
In vitro protocol:
1. Zhao Y, Zhang L, Yan A, Chen D, Xie R, Liu Y, Liang X, Zhao Y, Wei L, Yu J, Xu X, Su X. Grifolic acid induces GH3 adenoma cell death by inhibiting ATP production through a GPR120-independent mechanism. BMC Pharmacol Toxicol. 2018 May 30;19(1):26. doi: 10.1186/s40360-018-0215-4. PMID: 29843779; PMCID: PMC5975534.
In vivo protocol:
1. Zhao Y, Zhang H, Yan A, Zhu J, Liu K, Chen D, Xie R, Xu X, Su X. Grifolic acid induces mitochondrial membrane potential loss and cell death of RAW264.7 macrophages. Mol Med Rep. 2018 Feb;17(2):3281-3287. doi: 10.3892/mmr.2017.8218. Epub 2017 Dec 7. PMID: 29257254.
1: Zhao Y, Zhang L, Yan A, Chen D, Xie R, Liu Y, Liang X, Zhao Y, Wei L, Yu J, Xu X, Su X. Grifolic acid induces GH3 adenoma cell death by inhibiting ATP production through a GPR120-independent mechanism. BMC Pharmacol Toxicol. 2018 May 30;19(1):26. doi: 10.1186/s40360-018-0215-4. PubMed PMID: 29843779; PubMed Central PMCID: PMC5975534.
2: Zhao YF, Jiang F, Liang XY, Wei LL, Zhao YY, Ma Q, Hu YS, Su XL. Grifolic acid causes osteosarcoma cell death in vitro and in tumor-bearing mice. Biomed Pharmacother. 2018 Jul;103:1035-1042. doi: 10.1016/j.biopha.2018.04.132. Epub 2018 Apr 25. PubMed PMID: 29710661.
3: Taura F, Iijima M, Kurosaki F. Daurichromenic acid and grifolic acid: Phytotoxic meroterpenoids that induce cell death in cell culture of their producer Rhododendron dauricum. Plant Signal Behav. 2018 Jan 2;13(1):e1422463. doi: 10.1080/15592324.2017.1422463. Epub 2018 Jan 16. PubMed PMID: 29286881; PubMed Central PMCID: PMC5790407.
4: Zhao Y, Zhang H, Yan A, Zhu J, Liu K, Chen D, Xie R, Xu X, Su X. Grifolic acid induces mitochondrial membrane potential loss and cell death of RAW264.7 macrophages. Mol Med Rep. 2018 Feb;17(2):3281-3287. doi: 10.3892/mmr.2017.8218. Epub 2017 Dec 7. PubMed PMID: 29257254.
5: Grabovyi GA, Mohr JT. Total Synthesis of Grifolin, Grifolic Acid, LL-Z1272α, LL-Z1272β, and Ilicicolinic Acid A. Org Lett. 2016 Oct 7;18(19):5010-5013. Epub 2016 Sep 20. PubMed PMID: 27647101.
